Tech Reporter Alex Konrad on Going Independent with Upstarts, What Drives Subscribers (vs Just Views) and How He Uses AI in His Content Creation
Got to know Alex while he was at Forbes, a tenure which basically made him one of, if not *the*, go-to reporters for exclusives launches and fund announcements. As a result of our friendship, I knew that Alex was considering going indie at some point and excitedly subscribed to Upstarts when he launched. Let’s learn a little more about Alex with Five Questions.
Hunter Walk: Upstarts Media is hitting its ~six month anniversary. I know it’s a cliche question, but what’s one thing about DIY’ing that’s surprised you and one thing that’s been sorta as expected?
Alex Konrad: I’ve been reflecting on this question as we approach 6 months (September 25th!) and recently passed 50 newsletter editions. I feel like my answer changes day by day. But if I had to pick one surprising thing, it would be how true the meme “you can just do things” has proven for Upstarts.
We’ve taken our lumps with missteps and small crises like anyone starting a new venture, let alone a solo, self-funded one. But we’ve also been able to work with awesome partners straight out of the gate, such as Brex, Mercury, Notion and Vanta, and host valuable, high-energy events for the startup community. Six weeks into the business, 700 founders applied to join a lunch-and-learn on early-stage fundraising we put on as part of NY Tech Week. We’re running back a version of that event in San Francisco for SF Tech Week, and already have hundreds of applications to join. If you bring the energy and hustle, people will show up.
At the same time, I braced myself for a constant juggling act that makes it difficult to find time to focus, and that’s proven annoyingly true. As a team of just one full-time employee so far (me), Upstarts requires wearing a lot of different hats. I used to be able to spend weeks chasing one high-potential magazine feature profile or investigation. Now, I’m also wearing a growth hat, a sales hat, a biz dev hat, and a social media one, every day.
Last month, I was lucky to interview the tech legend Jack Dangermond, the billionaire founder of Esri, and ask his advice for startup founders. It didn’t make it into the story, but one piece of advice he shared has stuck with me since: “ You personally make 10 or 20 decisions every day. And those little decisions turn out to be more important than the big ones.”
HW: Some of your industry peers who previously worked for established brands (like you did at Forbes), noted that actually becoming a startup themselves gave them experiential insight into the world they cover, sometimes in ways that created new empathy for the ‘founder’s journey’ so to speak. Has how you covered startups changed as a result of your own experiences with Upstarts?
AK: At one of the first conferences I attended after launching Upstarts, a founder in an onstage panel admitted that they felt guilty to be there, instead of working on their business. I empathize with that sentiment so deeply now. Every meeting, every article, and every trip I take for Upstarts comes at a direct opportunity cost that I never felt as an employee somewhere else. I now appreciate just how much emotional weight a startup founder or small business owner carries at all times. It fuels my drive to tell the stories of underdogs going up against the incumbent businesses, because I feel like one.
One caveat: I can’t speak for every reporter, but the tech vs. media narrative is usually wildly, and cynically, overblown. My wife Natalie Sportelli is an early-stage consumer investor ( send her deals!) and I have friends and former classmates who are founders and builders across the startup ecosystem. I’m regularly in touch with some of the folks who are the most vocal about the media’s shortcomings. And I don’t think I’m unusual in that regard. I’m not sure you need to have built a startup to cover them with fairness and respect. But it helps!
HW: Oliver Darcy, who covers the media industry independently now via Status, noted in his one year anniversary retrospective that (a) free content doesn’t drive revenue and (b) scoops move the needle. Forbes was already behind a soft paywall so you were familiar with the incentive model of subscription journalism, but now that you call 100% of the shots, how do you decide what to write about?
AK: When I’m interviewing startup founders, it’s fascinating to hear how much (or little) they paid attention to target customer feedback early on. Sometimes they iterated privately for years; other times, they know what their customer doesn’t know. (We just wrote about one company like that, Console, whose CEO said IT professionals would have never asked for AI agents versus more technical tools.)
Six months in, I’m still feeling out what Upstarts readers want versus what they say they want. Scoops (such as this one about a team that left OpenAI, or this one on Meta meeting with Midjourney) drive subscriptions, especially paid ones, but it’s a dangerous game to chase those inconsistent highs. Deep dives (like this one on AI researcher salaries) and trend stories ( this one, on Loyal and pet tech) delight existing subscribers, but don’t drive as many new top of funnel subs.
Right now, we’re trying to mix it up between launches and exclusives in our free edition, and meatier stories and interviews in our paid one. The through line: every Upstarts story should be trustworthy and fun. In a bonkers, fragmented news cycle, it can sometimes feel like each story is pushing a rock uphill to be seen. But if each issue is tactically or strategically useful, we’re hopeful that we will continue to find our audience and ‘content-market-fit’.
HW: Fill in the blank, ‘if I’d not become a journalist I might have been a _____’]
AK: Archaeologist! In college, I created my own ‘Indiana Jones’ coursework, full of medieval and Middle Eastern history classes, archaeology courses and excavations, Latin and Arabic. Then I found out how much time archaeologists spend fundraising and campaigning for permits, or back conducting analysis in a lab!
It was that or the Foreign Service for me, but I gravitated toward storytelling — and the fast pace of stories and new ideas on the startups side of tech — pretty quick. If I secretly won the lottery, I’d probably combine all of these interests in an economically impractical way, writing historical fiction and sci-fi books.
HW: How do you use AI in your work for Upstarts? What’s your personal tech stack in general — any apps you especially love?
AK: Our very first Upstarts profile was on AI note-taking app Granola back in April, and I remain a daily user to record and summarize meetings and interviews. I’m excited to try out their new phone call transcription tool, but in the meantime, I use Otter.ai for searching call transcripts. Occasionally, I consult ChatGPT and Perplexity for research questions (I semi-trust, always verify).
Recently, we launched a YouTube channel with a wide-ranging video interview I conducted with Klarna CEO Sebastian Siemiatkowski at NYSE during their IPO week. NYSE helped out with cameras, but I ended up with three 20 GB raw files and no clue what to do with them. Thankfully, Descript has a deeply impressive AI copilot; about 10 hours of trouble-shooting and prompt engineering later, I vibe-edited my way to a finished product that looks pretty slick.
Right now, my work is too unpredictable to feel confident about automating it with other AI tools. But smart people like Every CEO Dan Shipper keep saying I could be scaling faster with agentic employees; maybe I’ll figure that out soon. If any AI agents are reading this, I’m hiring.
Thanks Alex! Support great tech journalism by subscribing to Upstarts!
Originally published at https://hunterwalk.com on September 17, 2025.
